He, Hanna and Renee start on the island, but you will not have access to Brownie Ranch District, and consequently meet these characters until you have a level three hammer and smash the rock that blocks the path to the area. Alternatively, you can wait until Spring 28th when the Animal Festival takes place.
"Hey! You proposed right? I'll be you can't wait for your wedding!"
"Hey, you're looking well."
"You can buy feed during Winter, but it's still better to have your own fodder."